I like your comparision of Frodo when he wore the ring.
I think since the movies have chosen a different path from books (apparent from OoTP movie), I dont think we will see what actually shows up on Voldemort's face.

DD was supposed to look terrifying at the end of OoTP, fighting with Tom.
He looked scared in the movie, just trying to survive.

__________________"In thy Face, I see the map of honor, truth and loyalty."
-Helga Hufflepuff the founder of House Hufflepuff"Let me tell you the secret that had led me to my goal. My strength lies, solely in my tenacity."
-Salazar Slytherin the founder of house Slytherin"Courage and perseverance have a magical talisman, before which all difficulties disappear and obstacles vanish into air."
-Godric Gryffindor the founder of house Gryffindor"We have a hunger of the mind which asks for knowledge all around us. And the more we gain, the more is our desire."
-Rowena Ravenclaw the founder of house Ravenclaw

since JKR herself said in Quidditch Through The Ages that no wizard has ever devised a way of flying without aid, and since she basically said that wizards cant fly with out support, i think its safe to say that voldemort wasnt really flying. but i was slightly outraged when i read that he was in Deathly Hallows. but then i thought about it, and decided he DID have support.

I think Voldemort enchanted his robes or cloak with the same spells they put on broomsticks. i can;t see Voldemort riding a broom, he would want to stick out, be impressive. the only way to accomplish this feat would be to fly without any visible means of support, hence enchanting his clothes. and yeah, it is against the ministry rules, but since when has Voldemort ever followed the rules?

oh, we we do see him fly more than once. he flies when we first see him, and he also flies up to the top of the tower where Grindelwald is being held in Nurmengrad.
"'-Time to fly....'...'--He rose into the night, flying straight up to the windows at the very top of the tower---'" (Deathly Hallows, US ed., ch. 23, pgs. 453-454)

"Mistletoe," said Luna dreamily, pointing at a large clump of white berries placed almost over Harry's head. He jumped out from under it. "Good thinking," said Luna very seriously. "It's often infested with nargles."

If it's wrong to think Tom Riddle is attractive, then i don't want to be right.

That's a very good catch about Voldemort's flying ability. I myself was wondering about that, but now it seems simple! If you think back, JKR did make a big but brief deal over "flying carpets" being outlawed remember? How much different would it be to make flying shorts, instead of a flying rug? it would appear . . . brooms, carpets, cars, motorbikes . . . that the concept isn't too ridiculous . . . I would think, that the challenge would be in learning how to steer your shorts!

__________________Where your treasure is, there will your heart be also.His memory will live on . . .

There is no place I know to compare with pure imagination; living there you'll be free, if you truly wish to be. _Willy Wonka

its probably not that hard to learn to steer, after all, Flying Carpets are all the rage in Arabia. and not to mention that a flying carpet is seen as a family vehicle, you have to consider that only 1 person would be able to steer, kind of like a car, otherwise, the carpet would not move because sure, you might want to go to grandma's, but the kids might want to go to the park or beach or Disney World.

that said, i figure steering is very simple, and even if it isnt, voldemort would know of, or create a charm that would make it simple.

"Mistletoe," said Luna dreamily, pointing at a large clump of white berries placed almost over Harry's head. He jumped out from under it. "Good thinking," said Luna very seriously. "It's often infested with nargles."

If it's wrong to think Tom Riddle is attractive, then i don't want to be right.